Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 15, Problem 59P
Furan undergoes electrophilic
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Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?
Compounds X and Y are both C7H15Cl products formed in the radical chlorination of 2,4-dimethylpentane.
Base-promoted E2 elimination of X and Y gives, in each case, a single C7H₁4 alkene.
Both X and Y undergo an SN2 reaction with sodium iodide in acetone solution to give C7H15l products; in this reaction Y reacts faster than X.
What is the structure of X?
• Do not use stereobonds in your answer.
• In cases where there is more than one possible structure for each molecule, just give one for each.
.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
на
11. See Fundamentals P167 for Figure 5.6
Use Figure 5.6 to rank the compounds in each of the following groups in order
of their reactivity toward electrophilic aromatic substitution:
(a) Nitrobenzene, phenol (hydroxybenzene), toluene
(b) Phenol, benzene, chlorobenzene, benzoic acid
(c) Benzene, bromobenzene, benzaldehyde, aniline (aminobenzene)
Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - Prob. 6PPCh. 15 - Prob. 7PPCh. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.10 The trifluoromethyl group...
Ch. 15 - PRACTICE PROBLEM 15.11
Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18
When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
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- For following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?arrow_forwardAlpha-phellandrene, C₁0H16, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C10H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: CHIC-CH HOCHSCHICH CH(CH3)2 Propose a structure for alpha-phellandrene.arrow_forwardAlpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?arrow_forward
- (a) Which is more reactive towards Electrophilic aromatic substitution (EAS)? (b) Which of the following is a a meta-substituted compound? (c) Which is the least reactive towards Electrophilic aromatic substitution (EAS)? (d) Which is an ortho-substituted compound?arrow_forwardت ا كل وخویه م اکتریار Q6/ Rank the compounds in each group in order of increasing reactivity in electrophilic aromatic substitution. NH NO2 b) O O Darrow_forwardRank the compounds in order of increasing reactivity in electrophilic aromatic substitution. Briefly explain your answer. CóH5OH, C6H5SO3H, C6H5CIarrow_forward
- Styrene (vinylbenzene) undergoes electrophilic aromatic substitution much faster thanbenzene, and the products are found to be primarily ortho- and para-substituted styrenes.Use resonance forms of the intermediates to explain these results.arrow_forwardCHEM 2252 Label the following compounds as aromatic, anti-aromatic, or non-aromatic (assume that all molecules are planar). In-class Assignment #4 Predict the product that would be formed when biphenyl reacts with a mixture of nitric and sulfuric acid. Draw a detailed, step-wise mechanism that shows formation of the electrophile and explains the observed regiochemistry. HNO3 H₂SO4arrow_forwardPlease don't provide handwriting solution Which of the following compounds can undergo nucleophilic aromatic substitution reactions?arrow_forward
- Define the below statement ? Benzene's six π electrons make it electron rich, so it reacts withelectrophiles.arrow_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?arrow_forwardThe sex attractant by which the female housefly attracts the male has the molecular formula C23H46. Catalytic hydrogenation yields an alkane of molecular formula C23H48. Ozonolysis yieldsWhat is the structure of the housefly sex attractant?arrow_forward
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